(3S,4S,6R)-3-ethenyl-6-[(S)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol

• ChemBase ID: 171253
• Molecular Formular: C20H24N2O3
• Molecular Mass: 340.41616
• Monoisotopic Mass: 340.17869264
• SMILES: c1(ccc2c(c1)c(ccn2)[C@@H]([C@@H]1N2CC[C@@H](C1)[C@@](C2)(O)C=C)O)OC
• Canonical SMILES: C=C[C@@]1(O)CN2CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cc(OC)cc2)O
• InChI: InChI=1S/C20H24N2O3/c1-3-20(24)12-22-9-7-13(20)10-18(22)19(23)15-6-8-21-17-5-4-14(25-2)11-16(15)17/h3-6,8,11,13,18-19,23-24H,1,7,9-10,12H2,2H3/t13-,18+,19-,20+/m0/s1
• InChIKey: BSRUJCFCZKMFMB-LGWHJFRWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,6R)-3-ethenyl-6-[(S)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol
• IUPAC Traditional name: (1S,3S,4S,6R)-3-ethenyl-6-[(S)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol
• Synonyms: (9S)-6’-Methoxy-Cinchonan-3,9-diol; (3S)-Hydroxyquinidine; 3-Hydroxyquinidine; (3S)-3-Hydroxy Quinidine

Database IDs

• CAS Number: 53467-23-5
• PubChem SID: 164227163
• PubChem CID: 13217486

CALCULATED PROPERTIES

• Acid pKa: 13.55172
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.3222476
• LogD (pH = 7.4): 0.4145601
• Log P: 1.6659791
• Molar Refractivity: 95.9137 cm^3
• Polarizability: 38.94357 Å^3
• Polar Surface Area: 65.82 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DCM; EtOAc; MeOH
• Apperance: White Solid
• Melting Point: 195-197°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H953230

The major metabolite of the Cinchona alkaloid Quinidine.

REFERENCES

• Small, D.L., et al.: J. Chem. Med., 22, 1014 (1979)
• Guentert, T.W., et al.: Eur. J. Drug Metab. Pharmacokinet., 7, 31 (1979)
• Rakhir, A., et al.: J. Pharmacokinet. Biopharm., 12, 1 (1979)
• Christie, D.J., et al.: J. Lab. Clin. Med., 112, 92 (1979)